What stands out worked out from the figures below

Windham has the most affordable homes ($210k median).

Milford has the most people working from home (14.5%).

What matters to you?

Pick a few. We’ll pull those rows to the top and mark which town comes out ahead on each. There’s no overall score: what matters is up to you.

Raising kidsAffordabilityOwning a homeShort commuteWorking from homeYounger crowdSettled, older crowdGrowing town

Measure	Windham	Milford
People
Population	23,961Lowest	30,431Highest
Growth since 20102010 → 2020 census	—	+8.5% U.S.: +7.4%
Median age	33.7±1.9Lowest 13% below U.S.	38.9±1.8Highest about the U.S. average
Kids under 18	20.1%±2.4Lowest U.S.: 22%	20.7%±2.4Highest U.S.: 22%
	Milford and Windham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	14.3%±1.9Lowest U.S.: 17.2%	18.8%±2Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	22.7%Lowest U.S.: 35.7%	35.3%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	15.2%±1.8Highest U.S.: 6.4%	3.9%±1.1Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$55,736±$5kLowest 31% below U.S.	$96,365±$4kHighest 19% above U.S.
Home valuemedian, owner-occupied	$209,800±$9kLowest 37% below U.S.	$476,700±$12kHighest 43% above U.S.
Rentmedian gross, monthly	$1,107±$69Lowest 22% below U.S.	$1,909±$137Highest 35% above U.S.
Property taxmedian, yearly	$4,633Lowest 49% above U.S.	$5,869Highest 88% above U.S.
Renters paying 30%+of income on rent	57.1%±8.1Highest U.S.: 51.1%	56.8%±8.5Lowest U.S.: 51.1%
	Windham and Milford are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	20.7%Highest U.S.: 12.5%	7.6%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	47.4%Lowest U.S.: 65.2%	65.2%Highest U.S.: 65.2%
Typical home builtmedian year	1956Lowest 24 yrs older than U.S.	1971Highest 9 yrs older than U.S.
Getting to work
Average commuteone way	24 minLowest 8% below U.S.	37 minHighest 40% above U.S.
Work from home	6.1%±1.7Lowest U.S.: 15.1%	14.5%±2.2Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#143 of 149 in CT	#213 of 282 in MA
School district	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS	Milford
High school in town	Windham High School	Milford High
Students per teacherat that high school	9.8Lowest	11.9Highest
On TownTapestry
Old photos in History	None yet	None yet

U.S. average · Sources: U.S. Census Bureau, American Community Survey 5-year estimates 2020–2024; 2010 & 2020 decennial census; NCES Common Core of Data. “±” is the Census margin of error. Property tax is top-coded by the Census at $10,000+. School rank compares math and reading proficiency against the state average.